Gastrol

Last updated
Gastrol
Gastrol.PNG
Names
Preferred IUPAC name
4-{[(4-Hydroxyphenyl)methoxy]methyl}-2-[(4-hydroxyphenyl)methyl]phenol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C21H20O4/c22-19-6-1-15(2-7-19)11-18-12-17(5-10-21(18)24)14-25-13-16-3-8-20(23)9-4-16/h1-10,12,22-24H,11,13-14H2
    Key: QBQNMIPDPJEZHR-UHFFFAOYSA-N
  • InChI=1/C21H20O4/c22-19-6-1-15(2-7-19)11-18-12-17(5-10-21(18)24)14-25-13-16-3-8-20(23)9-4-16/h1-10,12,22-24H,11,13-14H2
    Key: QBQNMIPDPJEZHR-UHFFFAOYAC
  • C1=CC(=CC=C1CC2=C(C=CC(=C2)COCC3=CC=C(C=C3)O)O)O
Properties
C21H20O4
Molar mass 336.387 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Gastrol is a phenolic compound produced by the saprophytic orchid Gastrodia elata . [1]

Related Research Articles

<span class="mw-page-title-main">Phenols</span> Chemical compounds in which hydroxyl group is attached directly to an aromatic ring

In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (−OH) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, C
6
H
5
OH
. Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule.

<span class="mw-page-title-main">Phenol</span> Organic compound (C6H5OH)

Phenol is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxy group. Mildly acidic, it requires careful handling because it can cause chemical burns.

<span class="mw-page-title-main">Phenyl group</span> Cyclic chemical group (–C₆H₅)

In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen, which may be replaced by some other element or compound to serve as a functional group. Phenyl group has six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Phenyl groups are commonplace in organic chemistry. Although often depicted with alternating double and single bonds, phenyl group is chemically aromatic and has equal bond lengths between carbon atoms in the ring.

<span class="mw-page-title-main">Peroxidase</span> Peroxide-decomposing enzyme

Peroxidases or peroxide reductases are a large group of enzymes which play a role in various biological processes. They are named after the fact that they commonly break up peroxides.

<span class="mw-page-title-main">Reimer–Tiemann reaction</span> Chemical reaction for ortho-formylation of phenols

The Reimer–Tiemann reaction is a chemical reaction used for the ortho-formylation of phenols; with the simplest example being the conversion of phenol to salicylaldehyde. The reaction was discovered by Karl Reimer and Ferdinand Tiemann. The Reimer in question was Karl Reimer (1845-1883) not the lesser known Carl Ludwig Reimer (1856-1921).

Phenolic is an adjective and a substantive (noun) that may apply to :

<span class="mw-page-title-main">Hydroxytyrosol</span> Chemical compound

Hydroxytyrosol is an organic compound with the formula (HO)2C6H3CH2CH2OH. Classified as a phenylethanoid, i.e. a relative of phenethyl alcohol. Its derivatives are found in a variety of natural sources, notably olive oils and wines. Hydroxytyrosol is a colorless solid, although samples often turn beige during storage. It is a derivative, formally speaking, of catechol.

<span class="mw-page-title-main">Folin–Ciocalteu reagent</span>

The Folin–Ciocâlteu reagent (FCR) or Folin's phenol reagent or Folin–Denis reagent, is a mixture of phosphomolybdate and phosphotungstate used for the colorimetric in vitro assay of phenolic and polyphenolic antioxidants, also called the gallic acid equivalence method (GAE). It is named after Otto Folin, Vintilă Ciocâlteu, and Willey Glover Denis. The Folin-Denis reagent is prepared by mixing sodium tungstate and phosphomolybdic acid in phosphoric acid. The Folin–Ciocalteu reagent is just a modification of the Folin-Denis reagent. The modification consisted of the addition of lithium sulfate and bromine to the phosphotungstic-phosphomolybdic reagent.

<i>Gastrodia</i> Genus of orchids

Gastrodia, commonly known as potato orchids or as 天麻属 , is a genus of terrestrial leafless orchids in the family Orchidaceae, about ninety of which have been described. Orchids in this genus have fleshy, upright stems and small to medium-sized resupinate flowers with narrow sepals and petals. They are native to Asia, Australia, New Zealand, central Africa, and various islands of the Indian and Pacific Oceans.

<i>Gastrodia elata</i> Species of plant

Gastrodia elata is a saprophytic perennial herb in the family Orchidaceae. It is found in Nepal, Bhutan, India, Japan, Korea, Siberia, Taiwan, and China.

<span class="mw-page-title-main">Alkylphenol</span> Family of organic compounds

Alkylphenols are a family of organic compounds obtained by the alkylation of phenols. The term is usually reserved for commercially important propylphenol, butylphenol, amylphenol, heptylphenol, octylphenol, nonylphenol, dodecylphenol and related "long chain alkylphenols" (LCAPs). Methylphenols and ethylphenols are also alkylphenols, but they are more commonly referred to by their specific names, cresols and xylenols.

<span class="mw-page-title-main">Phenolic content in wine</span> Wine chemistry

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

4-Hydroxybenzaldehyde is one of the three isomers of hydroxybenzaldehyde. It can be found in the orchids Gastrodia elata, Galeola faberi, and the Vanilla orchids.

<span class="mw-page-title-main">Syringic acid</span> Chemical compound

Syringic acid is a naturally occurring phenolic compound and dimethoxybenzene that is commonly found as a plant metabolite.

<span class="mw-page-title-main">Phenolic acid</span> Class of chemical compounds

Phenolic acids or phenolcarboxylic acids are types of aromatic acid compounds. Included in that class are substances containing a phenolic ring and an organic carboxylic acid function. Two important naturally occurring types of phenolic acids are hydroxybenzoic acids and hydroxycinnamic acids, which are derived from non-phenolic molecules of benzoic and cinnamic acid, respectively.

<span class="mw-page-title-main">Naturally occurring phenols</span> Group of chemical compounds

In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

<span class="mw-page-title-main">Gastrodin</span> Chemical compound

Gastrodin is a chemical compound which is the glucoside of gastrodigenin. It has been isolated from the orchid Gastrodia elata and from the rhizome of Galeola faberi. It can also be produced by biotransformation of 4-hydroxybenzaldehyde by Datura tatula cell cultures.

2,4-Bis(4-hydroxybenzyl)phenol is a phenolic compound produced by the saprophytic orchid Gastrodia elata and by the myco-heterotroph orchid Galeola faberi.

<span class="mw-page-title-main">Gastrodigenin</span> Chemical compound

Gastrodigenin is a phenolic compound found in the rhizome of Gastrodia elata.

<span class="mw-page-title-main">Drupanol</span> Chemical compound

Drupanol is a naturally occurring phenol that has been isolated from the seeds of Psoralea drupaceae. Although drupanol is sometimes said to be the same compound as bakuchiol, the two compounds are in fact distinct; they have the same molecular formula and weight but different chemical structures and hence are structural isomers. Bakuchiol has been found to possess antiandrogenic activity in vitro.

References

  1. Hayashi, Junko; Sekine, Toshikazu; Deguchi, Shigeyoshi; Lin, Qing; Horie, Syunji; Tsuchiya, Shizuko; Yano, Shingo; Watanabe, Kazuo; Ikegami, Fumio (2002). "Phenolic compounds from Gastrodia rhizome and relaxant effects of related compounds on isolated smooth muscle preparation". Phytochemistry. 59 (5): 513–9. doi:10.1016/S0031-9422(02)00008-0. PMID   11853746.